CZ299554B6 - Sloucenina se strukturou chinolonu, farmaceutickýprostredek ji obsahující a použití - Google Patents

Sloucenina se strukturou chinolonu, farmaceutickýprostredek ji obsahující a použití Download PDF

Info

Publication number: CZ299554B6
Authority: CZ; Czechia
Prior art keywords: methoxy; cyclopropyl; dihydro; oxo; compound
Prior art date: 1997-09-15

Application number

CZ20000931A

Other languages

Czech (cs)

English (en)

Other versions

CZ2000931A3 (cs

Inventor

Ledoussal@Benoir

Kim Almstead@Ji-In

Lyle Gray@Jeffrey

Eric Hu@Xiufeng

Original Assignee

The Procter & Gamble Company

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-09-15

Filing date

1998-09-15

Publication date

2008-09-03

1998-09-15 Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company

2000-08-16 Publication of CZ2000931A3 publication Critical patent/CZ2000931A3/cs

2008-09-03 Publication of CZ299554B6 publication Critical patent/CZ299554B6/cs

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 76
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 36
230000003287 optical effect Effects 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
-1 methoxy, methylthio Chemical group 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 14
208000015181 infectious disease Diseases 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
230000000813 microbial effect Effects 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000002265 prevention Effects 0.000 claims description 3
ZASYVQUJFRKPOO-UHFFFAOYSA-N 7-(3-aminopiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2CC(N)CCC2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 ZASYVQUJFRKPOO-UHFFFAOYSA-N 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
FUDKJNYIYARHMJ-UHFFFAOYSA-N 7-(3-amino-4-ethylpiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)C(CC)CCN1C1=CC=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1OC FUDKJNYIYARHMJ-UHFFFAOYSA-N 0.000 claims 1
YGFPIYYPDFYIGE-UHFFFAOYSA-N 7-(3-amino-4-methylpiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2CC(N)C(C)CC2)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 YGFPIYYPDFYIGE-UHFFFAOYSA-N 0.000 claims 1
AGPNGVLMDLSZJZ-UHFFFAOYSA-N 7-(5-amino-2-methylpiperidin-1-yl)-1-cyclopropyl-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(N2C(CCC(N)C2)C)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 AGPNGVLMDLSZJZ-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims 1
230000000845 anti-microbial effect Effects 0.000 abstract description 13
241000894006 Bacteria Species 0.000 abstract description 7
238000001228 spectrum Methods 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 57
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 26
239000000243 solution Substances 0.000 description 25
239000000047 product Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 21
238000000034 method Methods 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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230000000694 effects Effects 0.000 description 13
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000002585 base Substances 0.000 description 11
239000003242 anti bacterial agent Substances 0.000 description 10
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ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
239000000126 substance Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 9
230000000844 anti-bacterial effect Effects 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
230000003115 biocidal effect Effects 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
238000001914 filtration Methods 0.000 description 7
244000005700 microbiome Species 0.000 description 7
150000007660 quinolones Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
OKZIUSOJQLYFSE-UHFFFAOYSA-N difluoroboron Chemical compound F[B]F OKZIUSOJQLYFSE-UHFFFAOYSA-N 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
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239000012458 free base Substances 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
238000007911 parenteral administration Methods 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
229940111121 antirheumatic drug quinolines Drugs 0.000 description 5
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238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
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239000000725 suspension Substances 0.000 description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
BZHFSDYKFLNPST-UHFFFAOYSA-N 1-cyclopropyl-7-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(F)C=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 BZHFSDYKFLNPST-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
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239000012267 brine Substances 0.000 description 4
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238000001953 recrystallisation Methods 0.000 description 4
238000007086 side reaction Methods 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 3
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UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
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HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
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125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000001668 nucleic acid synthesis Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
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206010033072 otitis externa Diseases 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
GGPNYXIOFZLNKW-UHFFFAOYSA-N piperidin-3-amine;dihydrochloride Chemical compound Cl.Cl.NC1CCCNC1 GGPNYXIOFZLNKW-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
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239000003755 preservative agent Substances 0.000 description 1
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
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238000001243 protein synthesis Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000008213 purified water Substances 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000006798 recombination Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
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238000012552 review Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
208000013223 septicemia Diseases 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000010409 thin film Substances 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
230000014616 translation Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
229960003165 vancomycin Drugs 0.000 description 1
MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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239000000080 wetting agent Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Quinoline Compounds (AREA)

CZ20000931A 1997-09-15 1998-09-15 Sloucenina se strukturou chinolonu, farmaceutickýprostredek ji obsahující a použití CZ299554B6 (cs)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US5889197P	1997-09-15	1997-09-15
US13985998A	1998-08-25	1998-08-25

Publications (2)

Publication Number	Publication Date
CZ2000931A3 CZ2000931A3 (cs)	2000-08-16
CZ299554B6 true CZ299554B6 (cs)	2008-09-03

Family

ID=26738133

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ20000931A CZ299554B6 (cs)	1997-09-15	1998-09-15	Sloucenina se strukturou chinolonu, farmaceutickýprostredek ji obsahující a použití

Country Status (30)

Country	Link
US (3)	US6329391B1 (da)
EP (1)	EP1015445B1 (da)
JP (1)	JP4669607B2 (da)
KR (1)	KR100423778B1 (da)
CN (1)	CN1264837C (da)
AR (1)	AR013493A1 (da)
AT (1)	ATE423776T1 (da)
AU (1)	AU735186B2 (da)
BR (1)	BR9812644B1 (da)
CA (1)	CA2303389C (da)
CO (1)	CO4970702A1 (da)
CY (1)	CY1110255T1 (da)
CZ (1)	CZ299554B6 (da)
DE (1)	DE69840599D1 (da)
DK (1)	DK1015445T3 (da)
ES (1)	ES2321042T3 (da)
HU (1)	HUP0100051A3 (da)
ID (1)	ID24703A (da)
IL (2)	IL135036A0 (da)
MY (1)	MY138335A (da)
NO (1)	NO323563B1 (da)
NZ (1)	NZ503740A (da)
PE (1)	PE128799A1 (da)
PL (1)	PL339408A1 (da)
PT (1)	PT1015445E (da)
RU (1)	RU2193558C2 (da)
SA (1)	SA99191136B1 (da)
SK (1)	SK286420B6 (da)
TR (2)	TR200001435T2 (da)
WO (1)	WO1999014214A1 (da)

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NO323563B1 (no)	2007-06-11
IL135036A (en)	2007-12-03
US20090111851A1 (en)	2009-04-30
EP1015445A1 (en)	2000-07-05
HK1030415A1 (en)	2001-05-04
JP4669607B2 (ja)	2011-04-13
AU735186B2 (en)	2001-07-05
WO1999014214A1 (en)	1999-03-25
CO4970702A1 (es)	2000-11-07
CA2303389C (en)	2007-07-17
US6329391B1 (en)	2001-12-11
CY1110255T1 (el)	2015-01-14
DK1015445T3 (da)	2009-05-11
SK3812000A3 (en)	2000-09-12
SA99191136B1 (ar)	2006-07-30
US7482454B2 (en)	2009-01-27
US20060100436A1 (en)	2006-05-11
TR200505120T2 (tr)	2006-08-21
RU2193558C2 (ru)	2002-11-27
HUP0100051A2 (hu)	2001-10-28
AU9482998A (en)	1999-04-05
PL339408A1 (en)	2000-12-18
TR200001435T2 (tr)	2000-08-21
NZ503740A (en)	2002-09-27
SK286420B6 (sk)	2008-09-05
ATE423776T1 (de)	2009-03-15
PE128799A1 (es)	2000-02-17
CZ2000931A3 (cs)	2000-08-16
CA2303389A1 (en)	1999-03-25
BR9812644A (pt)	2001-12-18
DE69840599D1 (de)	2009-04-09
JP2001516756A (ja)	2001-10-02
IL135036A0 (en)	2001-05-20
MY138335A (en)	2009-05-29
PT1015445E (pt)	2009-05-14
AR013493A1 (es)	2000-12-27
ID24703A (id)	2000-08-03
US7868021B2 (en)	2011-01-11
HUP0100051A3 (en)	2002-08-28
ES2321042T3 (es)	2009-06-01
EP1015445B1 (en)	2009-02-25
NO20001340L (no)	2000-05-15
KR100423778B1 (ko)	2004-03-24
CN1278813A (zh)	2001-01-03
CN1264837C (zh)	2006-07-19
NO20001340D0 (no)	2000-03-15
KR20010024007A (ko)	2001-03-26
BR9812644B1 (pt)	2010-07-13

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Publication	Publication Date	Title
EP1015445B1 (en)	2009-02-25	Antimicrobial quinolones, their compositions and uses
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